Shawn Michaels’ Most Memorable Matches, Moments in WrestleMania History

Shawn Michaels’ Most Memorable Matches, Moments in WrestleMania History

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RICK SCUTERI/Associated Press

Known as Mr. WrestleMania, Shawn Michaels is arguably the greatest performer to ever step foot onto the Grandest Stage of Them All.

Although his WrestleMania record was a pedestrian 6-11, the Heartbreak Kid consistently captivated the WWE Universe with remarkable in-ring performances at the Showcase of the Immortals over the course of more than two decades.

His list of WrestleMania opponents reads like a who’s who of wrestling legends, including The Undertaker, John Cena, Ric Flair, Bret Hart, Kurt Angle, “Stone Cold” Steve Austin, Chris Jericho and even Vince McMahon.

Michaels was the common denominator in all those bouts, and there is no question that he helped author many of the greatest moments in WrestleMania history.

Here is a look at HBK’s greatest hits at WrestleMania.

HBK and Razor Ramon Popularize the Ladder Match at WrestleMania 10

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Although it wasn’t the first ladder match in pro wrestling history or even the first ladder match in WWE history, Michaels and Razor Ramon helped make the ladder match at WWE staple at WrestleMania 10.

The match, which took place at New York City’s Madison Square Garden, was months in the making with the Intercontinental Championship literally hanging in the balance.

HBK was the IC champion, but after taking a hiatus, Ramon was crowned the new titleholder. Michaels returned and claimed he was the real champion, which led to their WrestleMania 10 ladder match with two Intercontinental Championships suspended from the ceiling.

Michaels and Razor combined to put on what was one of the most innovative matches in WrestleMania history at that time.

Even though ladder matches are much different now, their match has stood the test of time and is still widely considered one of the best ladder matches ever.

Perhaps the best aspect of the bout was the fact that they only needed one ladder in order to make it through the entire match, whereas most current ladder matches feature several different ladders throughout.

While that ladder was nearly destroyed by the end of the contest, Michaels and Ramon made it work, and it added to the overall drama of the tilt.

One of the best things that can be said about the clash is that it felt like a regular singles match with a ladder involved rather than a gimmick match that needed the ladder in order to be good.

On a night that featured Bret Hart versus Owen Hart opening the show and Bret later closing the event by beating Yokozuna for the WWF Championship, Michaels and Ramon managed to steal the show.

That marked the first of many times HBK would accomplish that feat on the Grandest Stage of Them All.

After falling short in his attempt to win the WWF Championship from Diesel at WrestleMania 11, Michaels got another crack at the greatest prize in sports entertainment at WrestleMania 12.

HBK won his second consecutive Royal Rumble match, and his prize was the opportunity to compete in WWE’s first ever 60-minute Iron Man Match in the main event of WrestleMania against Bret “Hitman” Hart.

Michaels and Hart are considered two of the best in-ring workers in the history of the business, which made the Iron Man stipulation a perfect way to decide who the company’s leading man was at the time.

Although Michaels had never won the world title, he came close on numerous occasions, and the fans were very much behind him in his pursuit of the title.

Hart was a hugely popular face as well, though, which made for a unique dynamic that wasn’t often seen in wrestling during that time.

The match was littered with memorable WrestleMania moments, the first of which came during Michael’s entrance when he used a zip line to make his way to the ring.

While the early portion of the match was a feeling-out process, the second half of the contest picked up steam and showcased why Michaels and Hart are considered two of the best to ever grace the profession.

Sixty minutes was not enough to decide a winner, however, which resulted in commissioner Gorilla Monsoon announcing that there would be sudden-death overtime.

After a few more minutes, Michaels hit Hart with Sweet Chin Music to pick up the victory.

That set off a raucous celebration with HBK admiring the WWF Championship and Vince McMahon telling the viewers on commentary that Michaels’ boyhood dream had finally come true.

The Showstopper Retires Ric Flair at WrestleMania 24

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Many wrestling fans who grew up in the 1990s consider Michaels the greatest of all time, but it seems as though most wrestlers from HBK’s generation give that distinction to Ric Flair.

It isn’t often greats from separate eras get to do battle, but that is precisely what happened when Michaels and Flair went head to head at WrestleMania 24.

In the months leading up to WrestleMania, Flair’s career was on the line on multiple occasions, but he kept finding a way to win and avoid retirement.

His greatest challenge came at WrestleMania 24, as it was announced that he would have to beat Mr. WrestleMania himself in order to remain an active wrestler.

Flair was inducted into the WWE Hall of Fame the night before WrestleMania 24, and he then proceeded to have one of the best and most memorable matches of his career.

Although Flair was 59 years old at the time of the match, he showed plenty of flashes of his old self, and Michaels helped carry him through any potential rough patches.

Both Michaels and Flair have had better matches from a technical perspective, but the storytelling and raw emotion at WrestleMania 24 were difficult to top.

The most memorable aspect was undoubtedly the end when Michaels—prior to hitting his signature Sweet Chin Music—told Flair, “I’m sorry. I love you.”

With that, HBK laid out the Nature Boy and pinned him. As soon as the match was over, Michaels and Flair embraced in what was one of the most emotional displays ever seen at WrestleMania or any other wrestling event for that matter.

Michaels had great in-ring chemistry with several Superstars over the course of his career, but perhaps none of them clicked with him as well as The Undertaker.

The two legends had countless great matches with one another, however, their WrestleMania 25 bout reached another level of greatness, and it is deservedly in the conversation for being the best match of all time.

Michaels and Taker were both already surefire Hall of Famers with little to prove leading up to WrestleMania 25, but they managed to tell a compelling story that helped make their match one of the most highly anticipated contests on the card.

While The Deadman stood for darkness and fear, HBK represented light and hope, which was personified during his entrance, which featured Michaels dressed in all white, descending from the heavens.

The pageantry was matched only by the in-ring work with The Showstopper and The Phenom trying to top each other with each passing minute.

At one point, Taker went for a suicide dive over the top rope, which prompted Michaels to pull a cameraman into his path. The Undertaker contacted the cameraman but also nearly landed on his own head.

He still managed to continue the back-and-forth match, and it proceeded until Michaels made a major mistake in the latter stages.

Going for a moonsault, HBK was caught in midair by The Undertaker and spiked down with a Tombstone Piledriver, thus ending the match and extending Taker’s WrestleMania winning streak to 17-0.

The likes of Randy Orton, Batista and Edge posed true threats to The Undertaker’s streak in the years leading up to WrestleMania 25, but seemingly nobody came closer to ending it than Michaels.

The Deadman won, but Michaels left that show knowing he had taken part in arguably the greatest WrestleMania match of all time.

The Undertaker Retires Michaels at WrestleMania 26

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After falling just short of ending The Undertaker’s streak at WrestleMania 25, Michaels became obsessed with getting another crack at The Phenom at WrestleMania 26.

He lamented the mistake he made in losing to Taker the previous year, and he did everything he could think of to convince The Deadman to face him again.

Things came to a head at the Elimination Chamber pay-per-view when Michaels cost Taker the World Heavyweight Championship, resulting in Chris Jericho winning the title.

The Undertaker accepted Michaels’ challenge after that, but added the stipulation that HBK would be forced to retire if he lost again.

With Michaels’ career hanging in the balance, every moment of the WrestleMania 26 match was oozing with drama.

While Michaels isn’t best known as a submission specialist, he worked over Taker’s leg throughout the contest and targeted it with a number of different holds.

Michaels even did a moonsault onto The Undertaker’s injured leg through the announce table, thus putting the streak in serious jeopardy once again.

Taker kicked out of the Sweet Chin Music on multiple occasions, while HBK kicked out of the Tombstone, the chokeslam and even the Last Ride.

With Michaels fading and The Undertaker pleading with him to stay down, The Showstopper slapped The Deadman across the face.

That enraged The Undertaker and led to him finishing Michaels off with a jumping Tombstone, subsequently ending Mr. WrestleMania’s illustrious career.

The sadness of those in attendance was palpable, but when The Undertaker and Michaels shook hands out of respect, it was clear that HBK ended his career in the perfect way.